The biggest career wins often come with risk. On our series, The Big Bet, Chief speaks with some of the most powerful members in our network about that single moment when they bet on themselves — and won.

As one of just 26% of women who work in data and AI, Chief Member May Habib knows that the potential for AI can far outweigh its risks and concerns — if managed properly. That’s why, the CEO and Co-Founder of Writer, Inc., an AI writing assistant platform that’s raised $26 million in funding, says her goal is “to evaluate the entirety of corporate communication to tackle gender bias — and changing language is just the first step.”

“We can have a future where AI takes dignity away from a lot of people. Or, we can have a future where AI enables a lot more progress, access, and prosperity,” she says. “We’re working like hell for the latter.”

For this installment of The Big Bet, Habib shares how a love for language took her from banking executive to tech CEO, where she now runs a leading generative AI platform that’s used by Fortune 500 companies, including Spotify, Intuit, and Accenture. Today, with more content, programming, and even policies being written by AI, it’s imperative that intersectional leaders pave the way to ensure that our future isn’t built on the biases of our past — and Habib is up for the challenge.

On Transitioning From Banking to Entrepreneurship

“The common thread throughout my professional journey is my love for language. I earned my BA in Economics and Near Eastern Languages and Civilizations at Harvard University, where I was the Associate Managing Editor of The Harvard Crimson. I went into banking after college, working with tech companies in New York and then joined a sovereign wealth fund in the Middle East [called Mubadala Development Company], also investing in technology.

“It was only right for me to start my entrepreneurial journey in the language space. I first started working on NLP and machine translation problems in 2012, and then moved to San Francisco in 2015 to work on my first start up, a localization startup called Qordoba. In 2020, Qordoba became Writer.”

On Building an Inclusive Culture

“I’m a Lebanese Muslim first-generation immigrant and was also the first generation of my family to go to college. I’m very aware of who in the room might feel like an outsider and I make sure those people are given meaningful roles and responsibilities. I have a weird inclination to notice tiny social differences — honed probably from growing up among much wealthier kids — and I think as a result I’m very committed to building a culture at Writer that is only about ideas and contributions. We’re not cliquey. We’re probably all too different to be cliquey. Sixty percent of our leadership team are women, and 62% of our overall team are women or minorities of all types — ethnic, racial, LGBTQ+. I think we also have a lot more socioeconomic diversity than other tech startups and have a huge number of non-native English speakers too, though those aren’t things we measure. We value differences and that’s reflected in the makeup of the team.”

On Her Big Bet

“I was born into a family of entrepreneurs and hustlers. One of my earliest memories of being in Canada was watching my immigrant dad and uncle, whose family we lived with, buy used cars, fix them, and sell them. I worked in various family businesses and knew I was going to start a company one day. Once I had a problem space I was really excited about — language and tech — I took the plunge and started my first company.

“I started as an entrepreneur after several years in banking and private equity, which was a huge leap of faith. I was happy there and learning a lot, but I knew that the longer I did it, the longer my salary and bonuses would become golden handcuffs and I wouldn’t easily get out. And I wanted to have my entrepreneurial life kind of figured out before I had kids. So I kind of worked backwards and it was a ‘now or never’ jump.”

On Writer Existing Before ChatGPT

“We’ve been working on this stuff for years. In 2013, my Co-Founder and I were using machine learning to summarize big blocks of information. We both have a lot of years under our belt in natural language processing, AI-driven language generation, and the evolving ways we use language online. We’ve built two startups since then that focus on machine learning, deep learning models and language.”

I jokingly say that I’m a non-serial entrepreneur — I choose one space and stick to it for an unnaturally long time.
Chief Member May Habib, CEO and Co-Founder of Writer, Inc.

On Rooting Out Bias in AI

“The truth of the matter is, while AI is an incredible technology, most large language models learn from public information produced by humans, which means it includes human biases. As we use AI every day, we must address our own biases along with what we feed into AI. Without proper regulation, we'll surely regress on gender equality.

“Writer is designed to help establish healthy, inclusive communication in the workplace, including gender-neutral language. One of our customers, Ellevest, has incorporated guidelines into their company style guide to create an inclusive environment. For example, they've adjusted phrases like ‘working women’ to ‘women in the workforce,’ which prevents dismissing the unpaid work women do at home.

“From writing emails to performance reviews, there are subtle nuances that contain bias, and AI can help bring it to our attention. But we really need to evaluate the entirety of corporate communication to tackle gender bias — and changing language is just the first step. Companies need to support that change with policies that support employees and encourage inclusivity.”

On What Fuels Her

“Currently, I am fueled by the incredible advancements in AI. Our goal at Writer is to move past the fringe cases and arrive at impactful business use cases. We can have a future where AI takes dignity away from a lot of people. Or, we can have a future where AI enables a lot more progress, access, and prosperity. We’re working like hell for the latter.

“Personally, I am driven to come at things with a mindset of growth and learning. That mindset helps all of us be more successful throughout our careers, versus being anxious or desperate to get something done for clout or power. Folks at Writer have this insatiable need to constantly be resetting their learning curves. I love that.”

On Advice to Her Younger Self

“It will all work out.”

*Note: This interview has been edited and condensed for clarity.